| Identification | Back Directory | [Name]
N-T-BOC-PYRROLE | [CAS]
5176-27-2 | [Synonyms]
e-1-CarboxyL
ate(WX690266)
N-Boc-Pyrrole
1-Boc-pyrrole
N-T-BOC-PYRROLE
N-BOC-1H-PYRROLE
N-T-BOC-PYRROLE-1
N-Boc-pyrrole 98%
N-Boc-pyrrole
N-(t-Butoxycarbonyl)pyrrole
tert-butyl-pyrrole-carboxylate
TERT-BUTYL PYRROL-1-CARBOXYLATE
TERT-BUTYL 1-PYRROLECARBOXYLATE
tert-Butylpyrrole-1-carboxylate
N-tert-Butoxycarbonyl-1H-pyrrol
t-Butyl 1H-pyrrole-1-carboxylate
N-tert-Butoxycarbonyl-1H-pyrrole
N-(tert-butyloxycarbonyl)pyrrole
N-Boc-pyrrole, 97%, for synthesis
tert-butyl-pyrrole-carboxylate,98%
tert-butyl 1H-pyrrole-1-carboxylate
1-pyrrolecarboxylic acid tert-butyl ester
Pyrrole-1-carboxylic Acid tert-Butyl Ester
Tert-Butyl 1H-Pyrrole-1-Carboxylate(WX690266)
N-Boc-pyrrole,tert-Butyl 1-pyrrolecarboxylate
1H-Pyrrole-1-carboxylic acid, 1,1-diMethylethyl ester | [Molecular Formula]
C9H13NO2 | [MDL Number]
MFCD00209559 | [MOL File]
5176-27-2.mol | [Molecular Weight]
167.21 |
| Chemical Properties | Back Directory | [Boiling point ]
91-92 °C20 mm Hg(lit.)
| [density ]
1 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4685(lit.)
| [Fp ]
167 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Acetonitrile, Dichloromethane, Ethyl Acetate, Methanol, Tetrahydrofuran | [form ]
Solution | [pka]
-6.10±0.70(Predicted) | [color ]
Colorless to yellow | [InChI]
InChI=1S/C9H13NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H,1-3H3 | [InChIKey]
IZPYBIJFRFWRPR-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C=CC=C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3
| [HS Code ]
2933998090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
N-Boc-pyrrole was used in the synthesis of 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid by treating with n-BuLi and subsequent reaction with trimethyl borate.
It may be used as starting material in the synthesis of the following:
- tropane drivatives
- N-boc-2-(4-methoxyphenyl)pyrrole
- N-boc-pyrrol-2-ylboronic acid
| [Uses]
Pyrrole-1-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of pyrrole derived anti-cancer Agent. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 31, p. 764, 1966 DOI: 10.1021/jo01341a027 | [General Description]
N-Boc-pyrrole is an N-protected pyrrole. It undergoes Diels–Alder reaction with enantiomerically pure allene-1,3-dicarboxylates to form endo-adducts with retention in configurations at two newly generated stereogenic centers. It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane. Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported. | [Synthesis]
General procedure for the synthesis of tert-butyl 1-pyrrolecarboxylate from pyrrole and di-tert-butyl dicarbonate: di-tert-butyl dicarbonate (Boc2O, 9.8 g, 44.7 mmol) and triethylamine (TEA, 6.3 mL, 44.7 mmol) were added sequentially to a solution of pyrrole (3.0 g, 29.8 mmol) in dichloromethane (DCM, 15 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, extraction was performed with dichloromethane (2 x 400 mL) and water (400 mL). The organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to afford tert-butyl 1-pyrrolecarboxylate (26) as a white solid (7.5 g). Yield: 94%; 1H NMR (300 MHz, CDCl3) δ (ppm): 7.26 (s, 2H), 7.24 (t, J=2.4 Hz, 1H), 6.22 (t, J=2.4 Hz, 1H), 1.60 (d, J=11.7 Hz, 9H); ESI-MS [M+H]+=169.0. | [References]
[1] European Journal of Organic Chemistry, 2005, # 11, p. 2207 - 2212
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15739 - 15743
[3] Angew. Chem., 2015, vol. 127, # 52, p. 15965 - 15969,5
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1153 - 1164
[5] Medicinal Chemistry, 2018, vol. 14, # 5, p. 485 - 494 |
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